Abstract
A new and efficient synthetic process has been developed for preparation of 2-thioxoquinazolinone and quinazolinobenzothiazinedione derivatives. The related products were synthesized through reaction of isatoic anhydride, amines/anthranilic acids, and carbon disulfide (CS2) in the presence of potassium hydroxide in ethanol at reflux.
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Xia Y, Yang ZY, Hour MJ, Kuo SC, Xia P, Bastow KF, Nakanishi Y, Nampoothiri P, Hackl T, Hamel E, Lee KH (2001) Bioorg Med Chem Lett 11:193
Mukerji DD, Agarwal VR, Nautiyal SR (1985) Indian J Pharm Sci 47:8
Kenichi O, Yoshihisa Y, Toyonari O, Toru I, Yoshio I (1985) J Med Chem 28:568
Jiang JB, Hesson DP, Dusak BA, Dexter DL, Kang GJ, Hamel E (1990) J Med Chem 33:1721
Rajasekaran A, Rajamanickam V, Darlinquine S (2001) Yakugaku Zasshi 131:1079
Suesse M, Cleve D, Johne S (1990) Preparation of (3-alkoxycarbonylalkyl-3,4-dihydro-4-oxo-quinazolin-2-ylthio)alkanoic acids and esters as plant growth regulators and fungicides. Ger (East) DD 278788, May 16
Suesse M, Cleve D, Johne S (1991) Chem Abstr 114:62116y
Suesse M, Schaks A, Johne S (1990) Preparation of [(2-alkoxycarbonylalkylthio-3,4-dihydro-4-oxo-quinazolin-3-yl)alkanoyloxy]alkanoic acid esters as plant growth regulators and fungicides. Ger (East) DD 278789, May 16
Suesse M, Schaks A, Johne S (1991) Chem Abstr 114:62115
Lemaire C, Cantineau R, Guillaume M, Plenevaux A, Christiaens L (1991) J Nucl Med 32:2266
Saeed A, Shaheen U, Bolte M (2010) J Chin Chem Soc 57:82
Saeed A, Flörke U (2011) Crystals 1:254
Tiwari VK, Singh DD, Hussain HA, Mishra BB, Singh A (2008) Monatsh Chem 139:43
Dou GL, Wang MM, Huang ZB, Shi DQ (2009) J Heterocycl Chem 46:645
Castro A, Jerez MJ, Gil C, Calderón F, Doménech T, Nueda A, Martínez A (2008) Eur J Med Chem 43:1349
Azizian J, Mohammadi AA, Karimi AR (2003) Synth Commun 33:415
Satponth PS, Trivedi JP (1971) J Indian Chem Soc 48:1021
Lakhan R, Srivastava M (1993) Proc Indian Acad Sci Chem Sci 105:11
Singh S, Kaur S, Kaushal AN (1976) J Indian Chem Soc 53:382
Mahdavi M, Asadi M, Saeedi M, Rezaei Z, Moghbel H, Foroumadi A, Shafiee A (2012) Synlett 23:2521
Hosseini-Zare MS, Mahdavi M, Saeedi M, Asadi M, Javanshir S, Shafiee A, Foroumadi A (2012) Tetrahedron Lett 53:3448
Mahdavi M, Asadi M, Saeedi M, Ebrahimi M, Rasouli MA, Ranjbar PR, Foroumadi A, Shafiee A (2012) Synthesis 44:3649
Tahghighi A, Razmi S, Mahdavi M, Foroumadi P, Ardestani SK, Emami S, Kobarfard F, Dastmalchi S, Shafiee A, Foroumadi A (2012) Eur J Med Chem 50:124
Khalaj A, Nakhjiri M, Negahbani AS, Samadizadeh M, Firoozpour L, Rajabalian S, Samadi N, Faramarzi MA, Adipour N, Shafiee A, Foroumadi A (2011) Eur J Med Chem 46:65
Sunder S, Peet NP (1979) J Heterocycl Chem 16:1339
Wang M, Zhang TT, Liang Y, Gao JJ (2012) Monatsh Chem 143:835
Karimi-Jaberi Z, Arjmandi R (2011) Monatsh Chem 142:631
Mahdavi M, Asadi M, Saeedi M, Tehrani MH, Mirfazli SS, Shafiee A, Foroumadi A (2013) Synth Commun 43:2936
Clark RH, Wagner EC (1944) J Org Chem 9:55
Staiger RP, Wagner EC (1948) J Org Chem 13:347
Staiger RP, Miller EB (1959) J Org Chem 24:1214
Talukdar PB, Sengupta SK, Datta AK, Roy TK (1977) Indian J Chem B 15B:41
Wagner G, Rothe L (1969) Pharmazie 24:513
Shafik RM, Hazzaa AAB, Habib NS (1979) Pharmazie 34:148
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We gratefully acknowledge the partial financial support from Tehran University of Medicinal Sciences Research Council and Iran National Science Foundation (INSF).
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Asadi, M., Masoomi, S., Ebrahimi, S.M. et al. Convenient and sequential one-pot route for synthesis of 2-thioxoquinazolinone and quinazolinobenzothiazinedione derivatives. Monatsh Chem 145, 497–504 (2014). https://doi.org/10.1007/s00706-013-1110-8
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DOI: https://doi.org/10.1007/s00706-013-1110-8